There are projects that are easy enough for a smart startup founder to take on, and then there are projects that are simply too complex, and which require the help of an experienced lawyer. Financings, such as a seed round or convertible note financing, are definitely not DIY projects.
Several years ago, I bought a townhouse in Berkeley. There was no disposal in the kitchen, so I decided to install one. I went to Home Depot, and picked the one that had “Easiest To Install” printed on the box. It was about $65, so the price was right. Well, I learned that “easiest to install” does NOT mean “easy to install.” First, I couldn’t detach the drainpipe from the sink drain, and not being an experienced plumber, I didn’t know how much brute force I could apply without destroying the sink. So I called a plumber, and he took care of that, and installed the disposal under the sink. Then he pointed out that there was no electrical outlet for plugging in the disposal. I called an electrician to install a new outlet, and finally, two professionals and $300 later, my disposal worked. What I thought was an easy DIY project, because of what the box said, turned out to be not so easy or cheap after all. The problem was, I didn’t know what I didn’t know.
When it come to securities and corporate finance, the overwhelming majority of startup founders don’t know what they don’t know. Today I had a discussion with a very smart acquaintance about “friends and family” rounds. I pointed out that there’s no special exemption under securities laws for friends and family, and that when a startup raises money from them, generally the startup is violating the securities laws. Not only might the startup have to return all the investors money, but there could be civil and criminal penalties, as well as problems with later financing rounds. This was all news to him, and I bet it’s news to most startup founders.
Convertible note rounds aren’t simple, either. If you don’t understand all the moving parts, it is really easy to screw up. Do the startup founders read the reps and warranties in the note purchase agreement? Do they know why those reps and warranties are there, or what may happen if a rep turns out to be false? If the convertible note has a valuation cap, do you know about the liquidation preference overhang problem? Do you know how to fix it? Are you willing to pay me a few hundred dollars to save yourself a few hundred thousand dollars? How many startup founders know that they have to file a Form D with the SEC, as well as with the states where the startup and its investors are located, when doing a convertible note round? I imagine very few. There are even some startup lawyers I know of who routinely do not file a Form D after a seed round for their clients.
The bottom line is, when you are facing something where you might incur civil or criminal penalties, and which, if done wrong, can screw up your later attempts to get investment, you should invest in a good lawyer, and let him or her do it the right way. Because some projects, like investment rounds, are simply not DIY.